Holiday Homes in Pienza

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Pienza

Il Palazzetto
Relax in this open-plan living area with a patio offering a serene view of lush green surroundings.

Il Palazzetto

9.6 out of 10, Exceptional, (7)
Il Palazzetto
Villa Le Tortore Tuscany private luxury pool relax
Relax by the pool surrounded by a lush olive tree and comfortable seating.

Villa Le Tortore Tuscany private luxury pool relax

10.0 out of 10, Exceptional, (90)
"Very convenient to town and to surrounding wine regions - very good communication with host and was comfortable to stay for 3 people. Would stay again if in the area"
Villa Le Tortore Tuscany private luxury pool relax
Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga
Relax by the pool surrounded by lush greenery and a serene landscape view.

Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga

9.8 out of 10, Exceptional, (6)
"The villa was so comfortable and lovely. Michele was very responsive and helpful. 10/10 experience."
Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga
The Casetta di Brunello, quiet and breathtaking views
Traditional building with a rustic door, brass knocker, and wooden shutters.

The Casetta di Brunello, quiet and breathtaking views

9.6 out of 10, Exceptional, (15)
"Looking for a village away from the tourist crowds, this is it!"
The price is AU$433
includes taxes & fees
12 Aug - 13 Aug
The Casetta di Brunello, quiet and breathtaking views
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Traditional stone building with a charming outdoor seating area and balcony.

Casa Bacco - private house with a remarkable garden in the centre of Cortona

10.0 out of 10, Exceptional, (8)
"This home was outstanding from the moment we arrived. There were 6 adults and we had plenty of room to gather together. The courtyard is lovely for early morning coffee or evening wine. Close to everything that Cortona offers."
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Podere Casorbica with free parking, large garden, private pool.
Stunning roses bloom against a trellis in a lush, garden.

Podere Casorbica with free parking, large garden, private pool.

9.4 out of 10, Exceptional, (15)
"The property was lovely. Wifi was intermittently availble throughout our stay."
Podere Casorbica with free parking, large garden, private pool.
old barn on Via Francigena
Cozy bedroom with a neatly made bed, bedside table, and chair, set against a rustic brick ceiling and natural light.

old barn on Via Francigena

9.8 out of 10, Exceptional, (12)
" Very nice place and Sara just awesome"
old barn on Via Francigena
Spacious Luxury Apartment: pool, stunning views, 15-min walk from Siena center!
Relax by the serene pool surrounded by lush greenery and comfortable deck chairs.

Spacious Luxury Apartment: pool, stunning views, 15-min walk from Siena center!

9.6 out of 10, Exceptional, (32)
"Renting this villa was a relaxing, enjoyable way to experience Siena and the surrounding countryside. Lovely pool and grounds."
Spacious Luxury Apartment: pool, stunning views, 15-min walk from Siena center!
Air Conditioned 15th Century House with Pool on Wine Estate
Cozy living room with a fireplace, sofa set, and dining area featuring a kitchen with pendant lighting.

Air Conditioned 15th Century House with Pool on Wine Estate

10.0 out of 10, Exceptional, (66)
"Beautiful peaceful place to stay. Well stocked with everything we needed and comfortable living spaces."
Air Conditioned 15th Century House with Pool on Wine Estate
Casa Fontelunga, Tuscan holiday villa with private pool
Relax by the serene pool surrounded by lush greenery and comfortable seating options.

Casa Fontelunga, Tuscan holiday villa with private pool

9.2 out of 10, Wonderful, (9)
"We had a two week escape in the Tuscan countryside. We enjoyed touring around the area and a organized cooking class"
Casa Fontelunga, Tuscan holiday villa with private pool
La Dolce Collina
pool surrounded by lush gardens and multiple buildings with unique architectural styles.

La Dolce Collina

La Dolce Collina
Historic home in Montalcino
Cozy space with a stone wall, arched window, and traditional wooden furniture.

Historic home in Montalcino

10.0 out of 10, Exceptional, (3)
"Excellent host, clean home, beautifully appointed, and located in the heart of Montalcino. Walkable to grocery store and many restaurants."
Historic home in Montalcino
The Old Fashion House
Relax in this stylish living area with a sofa and dining table, featuring a kitchen with a stove and window.

The Old Fashion House

10.0 out of 10, Exceptional, (7)
"My husband and I spent a week here in April. We have been to Italy seven times, always staying in VRBO-type rentals and this rental stands apart as among the nicest. Recently renovated, well-equipped kitchen, balcony, comfortable heat, etc. You can see the owner, Giovanni, took great care with the design and remodeling. The location is perfect — just off the main street. We highly recommend this home! "
The Old Fashion House
Borgo Buio Town House, house in the historic center
Kitchen area with microwave, sink, and central island.

Borgo Buio Town House, house in the historic center

10.0 out of 10, Exceptional, (17)
"The hosts were very helpful and friendly and made our stay easy! The town of Montepulciano is very special and we would gladly stay again!"
Borgo Buio Town House, house in the historic center
Exclusive Stone Tower.
Enjoy dining and entertaining in this spacious kitchen with a large dining table, stove, and wine bottle and glasses.

Exclusive Stone Tower.

9.6 out of 10, Exceptional, (5)
"The tower was a perfect place for our trip to Tuscany! It had a ton of space with a full kitchen and living room. The town it is located in is fantastic. There is a small grocery store, a pizza place, and a fantastic restaurant where two people can get a delicious meal and drinks for about €30 all within walking distance. You can easily drive from the tower to Siena, Florence, Montalcino, Montepulciano, and I'm sure many other places that we didn't have time to get to. Sauro was a great host and...
The price is AU$298
includes taxes & fees
27 Aug - 28 Aug
Exclusive Stone Tower.
Buganza House - Ancient Umbrian Farmhouse
Relax by the serene pool surrounded by lush greenery.

Buganza House - Ancient Umbrian Farmhouse

10.0 out of 10, Exceptional, (6)
"Amazing property, old farmhouse, nice and cool at night. Pool was a lifesaver during long hot summer days. Good location to day trip to Rome or Florence!"
Buganza House - Ancient Umbrian Farmhouse
Borgo Santa Lucia, Casa Legnaia
Relax by the serene pool surrounded by lush greenery and a historic town view.

Borgo Santa Lucia, Casa Legnaia

Borgo Santa Lucia, Casa Legnaia
"Il gelsomino del Perugino" home with garden, a stone's throw from the center.
Enjoy a meal in our garden, surrounded by lush greenery and a beautifully set table for four.

"Il gelsomino del Perugino" home with garden, a stone's throw from the center.

10.0 out of 10, Exceptional, (2)
"Il gelsomino del Perugino" home with garden, a stone's throw from the center.
Apartment in Tuoro Near Lake Trasimeno
Relax by the clear blue pool surrounded by lush greenery and comfortable lounge chairs.

Apartment in Tuoro Near Lake Trasimeno

Apartment in Tuoro Near Lake Trasimeno
Charming house in historical Chianti Estate
Relax on the patio surrounded by lush flowers and comfortable seating.

Charming house in historical Chianti Estate

Charming house in historical Chianti Estate
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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